


Playing Dress-Up is Fun

by orphan_account



Category: Supernatural
Genre: Crossdressing, M/M, One Shot, Oral Sex, PWP
Language: English
Status: Completed
Published: 2013-11-17
Updated: 2013-11-17
Packaged: 2018-01-01 19:36:41
Rating: Explicit
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 562
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/1047777
Author URL: https://archiveofourown.org/users/orphan_account/pseuds/orphan_account
Summary: <blockquote class="userstuff">
              <p>Dean walks in on Kevin and gets some interesting ideas</p>
            </blockquote>





	Playing Dress-Up is Fun

**Author's Note:**

> I know Kevin is young, a lot younger than Dean, but he's not technically underage. if it bothers you anyway, do not continue reading

Kevin was in front of a mirror, tying the yellow bow on the back of his maid’s dress when Dean opened the door. 

“Hey man, what the hell? I thought I locked the door,” Kevin almost shouted.

“Sorry, about that…” Dean replied, “The locks in the bunker are pretty crappy. They’re actually the only crappy things here. I guess men of letters didn’t care much about privacy.” 

“Well can you leave?” Kevin asked, clearly embarrassed at having been caught dressing up as a maid.

“Why?” Dean asked, stepping through the doorway. Dean quirked an eyebrow and smiled. “You look sexy in that dress.” 

“Oh, stop it,” Kevin said as he glanced back of the mirror.

“Do you really want me to leave? Because I think it’d be a lot more fun if I stayed, even though I am a bit underdressed compared to you,” Dean said, gesturing to his plaid button-down and jeans. 

“Maybe you could get even more underdressed” Kevin said, embarrassed by his own dirty talk.

“That’s it, you’re finally playing along!” Dean perked up. He swooped in for a kiss. While Dean’s mouth explored Kevin’s, his hands traced along the frills and bow on the back of Kevin’s dress. He broke away from the kiss to start unbuttoning his own shirt, but never broke eye contact.

Kevin reached over to pull Dean’s shirt the rest of the way off and kissed his newly exposed shoulder. Then, he let his tongue trail across Dean’s body as he made his way to his lower lip.

Dean, clearly delighted, instructed Kevin to get onto the bed. Kevin happily obliged and lay down with his head propped up so he could still see Dean. Dean mounted the bed at the far end and bent over slightly. Standing on his knees with his legs spread apart over Kevin’s ankles, he used his right hand to creep all the way up to Kevin’s thigh. Then he pushed up the bottom of Kevin’s dress, revealing pink cotton panties. Dean was a bit surprised but very pleased.

“You like them?” Kevin asked, already knowing the answer based on Dean’s glowing facial expression.

“I most certainly do,” Dean said. “But it might be better if we take them off.”

“Well, if you say so,” Kevin said as he started to squirm a bit to help Dean slide them down to his ankles, not bothering even to get them all the way off.

Underneath, Kevin’s cock was hard and inviting. Dean bent over further and grabbed it in one hand and used his other hand to keep balance while he licked the tip slowly. 

One lick became a second and then a third, and then a long lick down the shaft, before putting it directly inside his warm mouth. His hand kept pumping for a bit as he sucked at the top half of Kevin’s cock, but soon that hand disappeared and he took his cock further into his mouth. Kevin started moaning, encouraging Dean to keep going.

Kevin watched as Dean’s head bobbed, giving him immense pleasure. His cock was tingling and he knew he was close to coming. Dean looked up for a moment while he was sucking and their eyes met and Kevin gasped as his cock started pouring into Dean’s mouth. 

Dean swallowed and looked up, smiling. “I think you should play dress-up more often.”


End file.
